Tetrahydropyridine insect repellent

ABSTRACT

Compounds of the formula D R A W I N G WHEREIN R is alkyl having one to four carbon atoms, alkoxy having one to four carbon atoms or halogen and their use as insect repellents.

United States Patent Baker [451 Feb. 11, 1975 TETRAHYDROPYRIDINE INSECTREPELLENT Don R. Baker, Orinda, Calif.

Staufier Chemical Company, New York, N.Y.

Filed: May 4, 1973 App]. No.: 357,151

Related US. Application Data Division of Ser. No. 225,272, Feb. 10,1972, Pat. No. 3,749,730.

Inventor:

Assignee:

References Cited UNITED STATES PATENTS 9/1965 Wragg et al 260/297 RPrimary Examiner-Vincent D. Turner Attorney, Agent, or Firm-Edwin H.Baker 57 ABSTRACT Compounds of the formula wherein R is alkyl having oneto four carbon atoms, alkoxy having one to four carbon atoms or halogenand their use as insect repellents.

5 Claims, N0 Drawings l TETRAHYDROPYRIDINE INSECT REPELLENT Thisapplication is a divisional of application Ser. No.

225,272, filed Feb. 10, 1972, now U.S. Pat. No. 3,749,730.

This invention relates to certain novel substituted benzoyl piperideinesand their use as insect repellents. The compounds of this invention havethe formula The compounds can be prepared by reacting a compound of theformula in which R is as defined with the compound 1,2,5,6tetrahydropyridene having the formula The 1,2,5,6 tetrahydropyridene isslowly added to a solution of the substituted benzoyl chloride in asolvent such as chloroform at a temperature under 30 C in the presenceof HCl acceptor such as triethylamine.

Preparation of the compounds of this invention is illustrated by thefollowing example EXAMPLE I l-(m-toluoyl)-l ,2,5 ,o-tetrahydropyridine7.7 grams (0.05 mole) in toluoyl chloride is dissolved in 100milliliters chloroform. 4.6 milliliters l,2,5,6 tetrahydropyridine and8.0 milliliters triethyl amine are added to the solution over a minuteperiod with cooling keeping the temperature under 30 C. The mixture isallowed to stand for 3 hours. The reaction product is recovered bywashing the mixture with 100 milliliters water and 100 milliliterssaturated Nal-lCO solution. The washed mixture is dried over MgSO, andevaporated to yield 10.5 grams of a compound corresponding to thedesired structure. bi -1.5530. The structure is confirmed by n.m.r.l-(o-fluorobenzoyl)- 1,2,5 ,6-tetrahydropyridine, l-( o-chl0robenzoyl)-1,2,5 ,6-tetrahydropyridine l-(p-bromobenzoyl)- 1,2,5,6-tetrahydropyridine, l-( p-butyl-benzoyl)- 1,2,5,6-tetrahydropyridine, l-(o-methoxybenzoyl)- 2l,2,5,6-tetrahydropyridine, and l-(m-butoxybenzoyl)-l,2,5,6-tetrahydropyridine are also prepared in a similar manner.according to the general method described for preparing the compounds ofthis invention.

The following test description and results illustrate the use of thecompounds of this invention as insect repellents.

HOUSE FLY REPELLENT TEST Eachtest cage consists of a tule-covered,number 116, 16 oz. waxed paper Dixie cup with two threefourths oz. waxedpaper condiment cups stapled on opposite sides of the upper, interiorperimeterfOne of the cups contains a sugar cube saturated with 0.8milliliters of acetone containing a specific concentration of the testrepellent and allowed to dry. The second condiment cup contains awater-saturated cotton plug. After each cube has been treated andallowed to dry, it is carefully weighed and placed in the test cage. Onehundred house flies of mixed sexes are then placed in the cages and allof the cages are placed on a 1 /2 rpm turntable. This procedure keepsthe flies in random distribution within the cage and eliminates theirgathering on the cage walls due to a phototropic response to outsidelight sources, which gathering has been found to give a false appearanceof repellency by the sugar cube. At daily intervals after treatment, theflies in each cage are anesthesized with C0 The cube is removed,reweighed and the percentage weight loss of the cube (due to consumptionby the flies) is recorded. The cubes with the least weight loss areconsidered to the most repellent to the flies. Table 1 contains asummary of the first, second, and fourth day readings for the candidaterepellent at 1% concentration.

TABLE 1 Percentage Weight Loss of Repellent Treated Sugar Cubes Due toConsumption by House Flies 1% Concentration 1. A method of repellinghouseflies comprising applying to the habitat thereof a repellent amountof a compound of the formula wherein R is alkyl having one to fourcarbon atoms. alkoxy having one to four carbon atoms or halogen. 2. Themethod of claim 1 where R is m-methyl. 3. The method of claim 1 where Ris o-fluoro. 4. The method of claim 1 wherein R is ochloro.

5. The method of claim 1 where R is m-methoxy. I1

1. A METHOD OF REPELLING HOUSEFLIES COMPRISING APPLYING TO THE HABITATTHEREOF A REPELLENT AMOUNT OF A COMPOUND OF THE FORMULA
 2. The method ofclaim 1 where R is m-methyl.
 3. The method of claim 1 where R iso-fluoro.
 4. The method of claim 1 wherein R is o-chloro.
 5. The methodof claim 1 where R is m-methoxy.